The number 5
Correct. A person sitting in a chair.
Correct. An oil lamp.
An oil lamp with a bent stem on the right side.
No, not that one. This shape is like a duck with a box on its back.
Correct. Now, a candle with wings.
No, that's a person. We want a tall, vertical shape with a pointed top and a pair of upward angled wings.
No, that shape has no wings. This shape has a pair of wings.
Now add the tall, vertical shape with a pointed top and a triangle base.
Close, but no. This shape has a pair of protrusions either side of the thinner central shape.

Outcome: unsuccessful
Speaker comments: I have no idea what the bot wants to hear for that last shape. A person would have understood any of the prompts I gave for it.